Methyl iodide → HCID 22724429, compound

HRID 2231065Notes

Reaction equation

HRID 2231065 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:12](=[O:13])[C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[N:10][C:9]3[CH:19]=[CH:20][CH:21]=[N:22][C:8]2=3)[CH:2]=1.IC.[C:31](=O)([O-])[O-].[K+].[K+].[Na]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:12](=[O:13])[C:11]([CH2:14][CH2:15][C:16]([O:18][CH3:31])=[O:17])=[N:10][C:9]3[CH:19]=[CH:20][CH:21]=[N:22][C:8]2=3)[CH:2]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5360545SodiumHCID 22724201HCID 22724201, compound

Product 1

HCID 22724429HCID 22724429, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-biphenylyl)-2-(2-carboxyethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine. (80 mg), iodomethane (0.04 ml) and potassium carbonate (90 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 1 hour. Then the mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonte. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was crystallized from methanol to give 4-(3-biphenylyl)-2-(2-methoxycarbonylethyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (71 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-0c0ab86b6e324558903774f628c65009
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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